# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 250831'
_audit_update_record             
;
2015-01-25 deposited with the CCDC.
2015-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          244-5
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H34 N2 O6'
_chemical_formula_weight         590.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.1550(10)
_cell_length_b                   23.851(5)
_cell_length_c                   11.944(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.18(3)
_cell_angle_gamma                90.00
_cell_volume                     1466.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11881
_cell_measurement_theta_min      1.71
_cell_measurement_theta_max      27.31

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9313
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_process_details   abscor

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-axis Rapid IP'
_diffrn_measurement_method       oscillation
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11881
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_sigmaI/netI    0.0902
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         27.31
_reflns_number_total             3297
_reflns_number_gt                1901
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0509P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3297
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1919(3) 0.15593(7) 0.77835(11) 0.0350(4) Uani 1 1 d . . .
O2 O -0.3558(3) 0.15327(8) 0.51330(13) 0.0404(5) Uani 1 1 d . . .
O3 O 0.5715(3) -0.06388(7) 0.32016(12) 0.0396(4) Uani 1 1 d . . .
N1 N 0.0406(3) 0.11890(7) 0.57213(14) 0.0269(4) Uani 1 1 d . . .
H1A H 0.1556 0.1190 0.6271 0.032 Uiso 1 1 calc R . .
C1 C 0.5022(6) 0.12986(14) 1.0676(2) 0.0572(9) Uani 1 1 d . . .
H1B H 0.5567 0.1679 1.0804 0.086 Uiso 1 1 calc R . .
H1C H 0.6465 0.1081 1.0446 0.086 Uiso 1 1 calc R . .
H1D H 0.4404 0.1145 1.1354 0.086 Uiso 1 1 calc R . .
C2 C 0.1909(7) 0.06867(12) 0.9538(3) 0.0639(9) Uani 1 1 d . . .
H2A H 0.0541 0.0687 0.8959 0.096 Uiso 1 1 calc R . .
H2B H 0.1272 0.0533 1.0213 0.096 Uiso 1 1 calc R . .
H2C H 0.3328 0.0462 0.9305 0.096 Uiso 1 1 calc R . .
C3 C 0.2840(5) 0.12841(11) 0.97547(18) 0.0360(6) Uani 1 1 d . . .
H3A H 0.1381 0.1508 0.9997 0.043 Uiso 1 1 calc R . .
C4 C 0.3842(4) 0.15455(11) 0.87090(17) 0.0318(5) Uani 1 1 d . . .
H4A H 0.4410 0.1925 0.8879 0.038 Uiso 1 1 calc R . .
H4B H 0.5339 0.1335 0.8487 0.038 Uiso 1 1 calc R . .
C5 C 0.0149(4) 0.19819(10) 0.76839(17) 0.0273(5) Uani 1 1 d . . .
C6 C -0.0002(5) 0.24187(10) 0.84462(19) 0.0337(6) Uani 1 1 d . . .
H6A H 0.1196 0.2439 0.9056 0.040 Uiso 1 1 calc R . .
C7 C -0.1918(5) 0.28252(10) 0.83083(19) 0.0355(6) Uani 1 1 d . . .
H7A H -0.1983 0.3117 0.8821 0.043 Uiso 1 1 calc R . .
C8 C -0.3734(5) 0.27984(10) 0.74128(19) 0.0356(6) Uani 1 1 d . . .
H8A H -0.5035 0.3067 0.7324 0.043 Uiso 1 1 calc R . .
C9 C -0.3579(5) 0.23652(10) 0.66523(18) 0.0316(5) Uani 1 1 d . . .
H9A H -0.4807 0.2345 0.6053 0.038 Uiso 1 1 calc R . .
C10 C -0.1644(4) 0.19579(9) 0.67520(17) 0.0256(5) Uani 1 1 d . . .
C11 C -0.1675(4) 0.15378(9) 0.58087(17) 0.0264(5) Uani 1 1 d . . .
C12 C 0.0853(4) 0.08286(9) 0.48232(16) 0.0247(5) Uani 1 1 d . . .
C13 C -0.0623(4) 0.08648(10) 0.38031(17) 0.0297(5) Uani 1 1 d . . .
H13A H -0.1970 0.1124 0.3723 0.036 Uiso 1 1 calc R . .
C14 C -0.0098(5) 0.05216(10) 0.29217(18) 0.0338(6) Uani 1 1 d . . .
H14A H -0.1092 0.0554 0.2251 0.041 Uiso 1 1 calc R . .
C15 C 0.1863(4) 0.01304(10) 0.30068(17) 0.0301(5) Uani 1 1 d . . .
H15A H 0.2179 -0.0100 0.2402 0.036 Uiso 1 1 calc R . .
C16 C 0.3372(4) 0.00825(9) 0.40055(17) 0.0254(5) Uani 1 1 d . . .
C17 C 0.2888(4) 0.04269(9) 0.49252(16) 0.0240(5) Uani 1 1 d . . .
C18 C 0.5449(4) -0.03541(9) 0.40371(17) 0.0264(5) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.360(3) . ?
O1 C4 1.443(2) . ?
O2 C11 1.228(2) . ?
O3 C18 1.221(3) . ?
N1 C11 1.366(3) . ?
N1 C12 1.404(3) . ?
C1 C3 1.529(3) . ?
C2 C3 1.521(4) . ?
C3 C4 1.512(3) . ?
C5 C6 1.388(3) . ?
C5 C10 1.408(3) . ?
C6 C7 1.387(3) . ?
C7 C8 1.383(3) . ?
C8 C9 1.381(3) . ?
C9 C10 1.392(3) . ?
C10 C11 1.507(3) . ?
C12 C13 1.403(3) . ?
C12 C17 1.421(3) . ?
C13 C14 1.372(3) . ?
C14 C15 1.375(3) . ?
C15 C16 1.392(3) . ?
C16 C17 1.405(3) . ?
C16 C18 1.493(3) . ?
C17 C18 1.478(3) 3_656 ?
C18 C17 1.478(3) 3_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C4 120.83(18) . . ?
C11 N1 C12 126.48(18) . . ?
C4 C3 C2 111.4(2) . . ?
C4 C3 C1 108.3(2) . . ?
C2 C3 C1 110.9(3) . . ?
O1 C4 C3 113.00(19) . . ?
O1 C5 C6 124.08(19) . . ?
O1 C5 C10 116.54(19) . . ?
C6 C5 C10 119.4(2) . . ?
C5 C6 C7 120.8(2) . . ?
C8 C7 C6 120.4(2) . . ?
C7 C8 C9 118.8(2) . . ?
C8 C9 C10 122.2(2) . . ?
C9 C10 C5 118.4(2) . . ?
C9 C10 C11 114.97(18) . . ?
C5 C10 C11 126.7(2) . . ?
O2 C11 N1 122.6(2) . . ?
O2 C11 C10 118.2(2) . . ?
N1 C11 C10 119.11(18) . . ?
C13 C12 N1 121.4(2) . . ?
C13 C12 C17 118.57(19) . . ?
N1 C12 C17 119.96(18) . . ?
C14 C13 C12 120.6(2) . . ?
C13 C14 C15 121.6(2) . . ?
C14 C15 C16 119.5(2) . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 C18 116.41(19) . . ?
C17 C16 C18 123.11(18) . . ?
C16 C17 C12 119.31(18) . . ?
C16 C17 C18 117.86(19) . 3_656 ?
C12 C17 C18 122.84(19) . 3_656 ?
O3 C18 C17 122.3(2) . 3_656 ?
O3 C18 C16 118.69(18) . . ?
C17 C18 C16 119.02(19) 3_656 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O3 0.86 2.00 2.663(2) 132.9 3_656
N1 H1A O1 0.86 2.01 2.691(2) 135.6 .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.31
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.133
